Palladium(II) Complexes of Substituted Salicylaldehydes: Synthesis, Characterization and Investigation of Their Biological Profile
Five palladium(II) complexes of substituted salicylaldehydes (X-saloH, X = 4-Et<sub>2</sub>N (for <b>1</b>), 3,5-diBr (for <b>2</b>), 3,5-diCl (for <b>3</b>), 5-F (for <b>4</b>) or 4-OMe (for <b>5</b>)) bearing the general formu...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-07-01
|
| Series: | Pharmaceuticals |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1424-8247/15/7/886 |
| _version_ | 1797444418036301824 |
|---|---|
| author | Ariadni Zianna George Geromichalos Augusta-Maria Fiotaki Antonios G. Hatzidimitriou Stavros Kalogiannis George Psomas |
| author_facet | Ariadni Zianna George Geromichalos Augusta-Maria Fiotaki Antonios G. Hatzidimitriou Stavros Kalogiannis George Psomas |
| author_sort | Ariadni Zianna |
| collection | DOAJ |
| description | Five palladium(II) complexes of substituted salicylaldehydes (X-saloH, X = 4-Et<sub>2</sub>N (for <b>1</b>), 3,5-diBr (for <b>2</b>), 3,5-diCl (for <b>3</b>), 5-F (for <b>4</b>) or 4-OMe (for <b>5</b>)) bearing the general formula [Pd(X-salo)<sub>2</sub>] were synthesized and structurally characterized. The crystal structure of complex [Pd(4-Et<sub>2</sub>N-salo)<sub>2</sub>] was determined by single-crystal X-ray crystallography. The complexes can scavenge 1,1-diphenyl-picrylhydrazyl and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and reduce H<sub>2</sub>O<sub>2</sub>. They are active against two Gram-positive (<i>Staphylococcus aureus</i> and <i>Bacillus subtilis</i>) and two Gram-negative (<i>Escherichia coli</i> and <i>Xanthomonas campestris</i>) bacterial strains. The complexes interact strongly with calf-thymus DNA via intercalation, as deduced by diverse techniques and via the determination of their binding constants. Complexes interact reversibly with bovine and human serum albumin. Complementary insights into their possible mechanisms of bioactivity at the molecular level were provided by molecular docking calculations, exploring in silico their ability to bind to calf-thymus DNA, <i>Escherichia coli</i> and <i>Staphylococcus aureus</i> DNA-gyrase, 5-lipoxygenase, and membrane transport lipid protein 5-lipoxygenase-activating protein, contributing to the understanding of the role complexes <b>1</b>–<b>5</b> can play both as antioxidant and antibacterial agents. Furthermore, in silico predictive tools have been employed to study the chemical reactivity, molecular properties and drug-likeness of the complexes, and also the drug-induced changes of gene expression profile (as protein- and mRNA-based prediction results), the sites of metabolism, the substrate/metabolite specificity, the cytotoxicity for cancer and non-cancer cell lines, the acute rat toxicity, the rodent organ-specific carcinogenicity, the anti-target interaction profiles, the environmental ecotoxicity, and finally the activity spectra profile of the compounds. |
| first_indexed | 2024-03-09T13:11:22Z |
| format | Article |
| id | doaj.art-28a2e4ec4ec34b8fadd2674f8d0affb5 |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-09T13:11:22Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-28a2e4ec4ec34b8fadd2674f8d0affb52023-11-30T21:40:45ZengMDPI AGPharmaceuticals1424-82472022-07-0115788610.3390/ph15070886Palladium(II) Complexes of Substituted Salicylaldehydes: Synthesis, Characterization and Investigation of Their Biological ProfileAriadni Zianna0George Geromichalos1Augusta-Maria Fiotaki2Antonios G. Hatzidimitriou3Stavros Kalogiannis4George Psomas5Laboratory of Inorganic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, GR-54124 Thessaloniki, GreeceLaboratory of Inorganic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, GR-54124 Thessaloniki, GreeceDepartment of Nutritional Sciences and Dietetics, International Hellenic University, Sindos, GR-57400 Thessaloniki, GreeceLaboratory of Inorganic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, GR-54124 Thessaloniki, GreeceDepartment of Nutritional Sciences and Dietetics, International Hellenic University, Sindos, GR-57400 Thessaloniki, GreeceLaboratory of Inorganic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, GR-54124 Thessaloniki, GreeceFive palladium(II) complexes of substituted salicylaldehydes (X-saloH, X = 4-Et<sub>2</sub>N (for <b>1</b>), 3,5-diBr (for <b>2</b>), 3,5-diCl (for <b>3</b>), 5-F (for <b>4</b>) or 4-OMe (for <b>5</b>)) bearing the general formula [Pd(X-salo)<sub>2</sub>] were synthesized and structurally characterized. The crystal structure of complex [Pd(4-Et<sub>2</sub>N-salo)<sub>2</sub>] was determined by single-crystal X-ray crystallography. The complexes can scavenge 1,1-diphenyl-picrylhydrazyl and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and reduce H<sub>2</sub>O<sub>2</sub>. They are active against two Gram-positive (<i>Staphylococcus aureus</i> and <i>Bacillus subtilis</i>) and two Gram-negative (<i>Escherichia coli</i> and <i>Xanthomonas campestris</i>) bacterial strains. The complexes interact strongly with calf-thymus DNA via intercalation, as deduced by diverse techniques and via the determination of their binding constants. Complexes interact reversibly with bovine and human serum albumin. Complementary insights into their possible mechanisms of bioactivity at the molecular level were provided by molecular docking calculations, exploring in silico their ability to bind to calf-thymus DNA, <i>Escherichia coli</i> and <i>Staphylococcus aureus</i> DNA-gyrase, 5-lipoxygenase, and membrane transport lipid protein 5-lipoxygenase-activating protein, contributing to the understanding of the role complexes <b>1</b>–<b>5</b> can play both as antioxidant and antibacterial agents. Furthermore, in silico predictive tools have been employed to study the chemical reactivity, molecular properties and drug-likeness of the complexes, and also the drug-induced changes of gene expression profile (as protein- and mRNA-based prediction results), the sites of metabolism, the substrate/metabolite specificity, the cytotoxicity for cancer and non-cancer cell lines, the acute rat toxicity, the rodent organ-specific carcinogenicity, the anti-target interaction profiles, the environmental ecotoxicity, and finally the activity spectra profile of the compounds.https://www.mdpi.com/1424-8247/15/7/886palladium(II)substituted salicylaldehydesantioxidant activityantimicrobial activityinteraction with DNAinteraction with serum albumins |
| spellingShingle | Ariadni Zianna George Geromichalos Augusta-Maria Fiotaki Antonios G. Hatzidimitriou Stavros Kalogiannis George Psomas Palladium(II) Complexes of Substituted Salicylaldehydes: Synthesis, Characterization and Investigation of Their Biological Profile Pharmaceuticals palladium(II) substituted salicylaldehydes antioxidant activity antimicrobial activity interaction with DNA interaction with serum albumins |
| title | Palladium(II) Complexes of Substituted Salicylaldehydes: Synthesis, Characterization and Investigation of Their Biological Profile |
| title_full | Palladium(II) Complexes of Substituted Salicylaldehydes: Synthesis, Characterization and Investigation of Their Biological Profile |
| title_fullStr | Palladium(II) Complexes of Substituted Salicylaldehydes: Synthesis, Characterization and Investigation of Their Biological Profile |
| title_full_unstemmed | Palladium(II) Complexes of Substituted Salicylaldehydes: Synthesis, Characterization and Investigation of Their Biological Profile |
| title_short | Palladium(II) Complexes of Substituted Salicylaldehydes: Synthesis, Characterization and Investigation of Their Biological Profile |
| title_sort | palladium ii complexes of substituted salicylaldehydes synthesis characterization and investigation of their biological profile |
| topic | palladium(II) substituted salicylaldehydes antioxidant activity antimicrobial activity interaction with DNA interaction with serum albumins |
| url | https://www.mdpi.com/1424-8247/15/7/886 |
| work_keys_str_mv | AT ariadnizianna palladiumiicomplexesofsubstitutedsalicylaldehydessynthesischaracterizationandinvestigationoftheirbiologicalprofile AT georgegeromichalos palladiumiicomplexesofsubstitutedsalicylaldehydessynthesischaracterizationandinvestigationoftheirbiologicalprofile AT augustamariafiotaki palladiumiicomplexesofsubstitutedsalicylaldehydessynthesischaracterizationandinvestigationoftheirbiologicalprofile AT antoniosghatzidimitriou palladiumiicomplexesofsubstitutedsalicylaldehydessynthesischaracterizationandinvestigationoftheirbiologicalprofile AT stavroskalogiannis palladiumiicomplexesofsubstitutedsalicylaldehydessynthesischaracterizationandinvestigationoftheirbiologicalprofile AT georgepsomas palladiumiicomplexesofsubstitutedsalicylaldehydessynthesischaracterizationandinvestigationoftheirbiologicalprofile |